##############################################################################
###                                                                        ###
###        Electronic paper (Acta Crystallographica Section E)             ###
###                                                                        ###
##############################################################################
#                                                                            #
# This CIF contains the data in a paper accepted for publication in Acta     #
# Crystallographica Section E. It conforms to the requirements of Notes      #
# for Authors for Section E, and has been peer reviewed under the auspices   #
# of the IUCr Commission on Journals.                                        #
#                                                                            #
# Full details of the Crystallographic Information File format               #
# are given in the paper "The Crystallographic Information File (CIF):       #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H.      #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685].                  #
#                                                                            #
# The current version of the core CIF dictionary is obtainable from          #
# ftp://ftp.iucr.org/pub/cif_core.dic. The current version number is 2.4.    #
#                                                                            #
# Software is freely available for graphical display of the structure(s) in  #
# this CIF.  For information consult the CIF home page http://www.iucr.org/  #
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data_I
_audit_creation_method     SHELXL-97
_chemical_name_systematic
;
(1R,1'R,3S,3'S)-5,5',10,10'-Tetramethoxy-1,1',3,3'-
tetramethyl-
3,3',4,4'-tetrahydro-1H,1'H-8,8'-bi[benzo[g]isochromene]
;
_chemical_name_common     ?
_chemical_formula_moiety     'C34 H38 O6'
_chemical_formula_sum     'C34 H38 O6'
_chemical_formula_weight     542.64
_chemical_melting_point     '541.15'
_symmetry_cell_setting     'orthorhombic'
_symmetry_space_group_name_H-M     'C 2 2 21'
_symmetry_space_group_name_hall     'C 2c 2'
loop_
    _symmetry_equiv_pos_as_xyz
    'x, y, z'
    '-x, -y, z+1/2'
    'x, -y, -z'
    '-x, y, -z+1/2'
    'x+1/2, y+1/2, z'
    '-x+1/2, -y+1/2, z+1/2'
    'x+1/2, -y+1/2, -z'
    '-x+1/2, y+1/2, -z+1/2'
_cell_length_a     8.8773(2)
_cell_length_b     13.9298(2)
_cell_length_c     23.1234(4)
_cell_angle_alpha     90.00
_cell_angle_beta     90.00
_cell_angle_gamma     90.00
_cell_volume     2859.42(9)
_cell_formula_units_Z     4
_cell_measurement_reflns_used     4238
_cell_measurement_theta_min     1.76
_cell_measurement_theta_max     28.56
_cell_measurement_temperature     89(2)
_exptl_crystal_description     needle
_exptl_crystal_colour     'pale yellow'
_exptl_crystal_size_max     0.36
_exptl_crystal_size_mid     0.28
_exptl_crystal_size_min     0.22
_exptl_crystal_density_diffrn     1.261
_exptl_crystal_density_meas     ?
_exptl_crystal_density_method     'not measured'
_exptl_crystal_F_000     1160
_exptl_absorpt_coefficient_mu     0.085
_exptl_absorpt_correction_type     multi-scan
_exptl_absorpt_process_details     '(SADABS; Bruker, 2001)'
_exptl_absorpt_correction_T_min     0.889
_exptl_absorpt_correction_T_max     0.981
_diffrn_ambient_temperature     89(2)
_diffrn_radiation_type     MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source     'fine-focus sealed tube'
_diffrn_radiation_monochromator     graphite
_diffrn_measurement_device_type     'Siemens SMART CCD'
_diffrn_measurement_method     'ω scans'
_diffrn_reflns_number     22789
_diffrn_reflns_av_R_equivalents     0.0517
_diffrn_reflns_av_sigmaI/netI     0.0506
_diffrn_reflns_theta_min     1.76
_diffrn_reflns_theta_max     28.56
_diffrn_reflns_theta_full     28.56
_diffrn_measured_fraction_theta_max     0.996
_diffrn_measured_fraction_theta_full     0.996
_diffrn_reflns_limit_h_min     -11
_diffrn_reflns_limit_h_max     11
_diffrn_reflns_limit_k_min     -18
_diffrn_reflns_limit_k_max     18
_diffrn_reflns_limit_l_min     -27
_diffrn_reflns_limit_l_max     30
_diffrn_standards_number     0
_diffrn_standards_interval_count     .
_diffrn_standards_interval_time     .
_diffrn_standards_decay_%     ?
_refine_special_details
;
Refinement of F² against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F², conventional
R-factors R are based on F, with F set to zero for
negative F². The threshold expression of F² >
σ(F²) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F² are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total     2035
_reflns_number_gt     1542
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef     Fsqd
_refine_ls_matrix_type     full
_refine_ls_R_factor_all     0.0654
_refine_ls_R_factor_gt     0.0403
_refine_ls_wR_factor_gt     0.0871
_refine_ls_wR_factor_ref     0.0952
_refine_ls_goodness_of_fit_ref     1.125
_refine_ls_restrained_S_all     1.125
_refine_ls_number_reflns     2035
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment     constr
_refine_ls_weighting_scheme     calc
_refine_ls_weighting_details
         'calc w=1/[σ²(Fo²)+(0.0484P)²+0.1354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens     geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary     difmap
_refine_ls_shift/su_max     0.000
_refine_ls_shift/su_mean     0.000
_refine_diff_density_max     0.213
_refine_diff_density_min     -0.189
_refine_ls_extinction_method     none
_refine_ls_extinction_coef     ?
loop_
    _atom_type_symbol
    _atom_type_description
    _atom_type_scat_dispersion_real
    _atom_type_scat_dispersion_imag
    _atom_type_scat_source
    'C' 'C' 0.0033 0.0016
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'H' 'H' 0.0000 0.0000
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
    'O' 'O' 0.0106 0.0060
                         'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection     'SMART (Siemens, 1995)'
_computing_cell_refinement     'SAINT (Siemens, 1995)'
_computing_data_reduction     'SAINT (Siemens, 1995)'
_computing_structure_solution     'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement     'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics
  'ORTEPIII (Burnett & Johnson, 1996) and Mercury (Macrae et al.,  2006)'
_computing_publication_material     'publCIF (Westrip, 2008)'
loop_
    _atom_site_type_symbol
    _atom_site_label
    _atom_site_fract_x
    _atom_site_fract_y
    _atom_site_fract_z
    _atom_site_U_iso_or_equiv
    _atom_site_adp_type
    _atom_site_calc_flag
    _atom_site_refinement_flags
    _atom_site_occupancy
    _atom_site_disorder_assembly
    _atom_site_disorder_group
    O O2 0.81372(17) 0.37827(10) 0.59844(6) 0.0305(4) Uani d . 1 . .
    O O1 0.33079(16) 0.12481(10) 0.60649(6) 0.0293(4) Uani d . 1 . .
    O O3 0.29982(17) 0.39411(11) 0.69152(7) 0.0340(4) Uani d . 1 . .
    C C4 0.7076(2) 0.22511(15) 0.57426(9) 0.0249(5) Uani d . 1 . .
    C C2 0.8442(2) 0.11042(16) 0.51523(9) 0.0264(5) Uani d . 1 . .
    H H2 0.9313 0.0936 0.4953 0.032 Uiso calc R 1 . .
    C C1 0.7206(2) 0.04620(15) 0.51579(8) 0.0240(5) Uani d . 1 . .
    C C9 0.4425(2) 0.27435(16) 0.63512(9) 0.0259(5) Uani d . 1 . .
    C C5 0.5831(2) 0.16126(15) 0.57533(9) 0.0235(4) Uani d . 1 . .
    C C7 0.6948(2) 0.31407(15) 0.60336(9) 0.0260(5) Uani d . 1 . .
    C C3 0.8384(2) 0.19642(15) 0.54331(9) 0.0257(5) Uani d . 1 . .
    H H3 0.9215 0.2370 0.5422 0.031 Uiso calc R 1 . .
    C C10 0.4513(2) 0.18827(15) 0.60595(9) 0.0254(5) Uani d . 1 . .
    C C6 0.5934(2) 0.07262(14) 0.54638(9) 0.0243(5) Uani d . 1 . .
    H H6 0.5122 0.0305 0.5479 0.029 Uiso calc R 1 . .
    C C11 0.5454(3) 0.43732(15) 0.65890(10) 0.0312(5) Uani d . 1 . .
    H H11A 0.6029 0.4843 0.6372 0.037 Uiso calc R 1 . .
    H H11B 0.5819 0.4371 0.6984 0.037 Uiso calc R 1 . .
    C C8 0.5659(2) 0.33918(16) 0.63246(9) 0.0267(5) Uani d . 1 . .
    C C13 0.2982(3) 0.29950(16) 0.66695(9) 0.0314(5) Uani d . 1 . .
    H H13 0.2144 0.2957 0.6395 0.038 Uiso calc R 1 . .
    C C12 0.3790(3) 0.46387(17) 0.65792(10) 0.0354(6) Uani d . 1 . .
    H H12 0.3422 0.4622 0.6180 0.043 Uiso calc R 1 . .
    C C17 0.3459(3) 0.56069(17) 0.68390(11) 0.0430(7) Uani d . 1 . .
    H H17A 0.2397 0.5733 0.6816 0.065 Uiso calc R 1 . .
    H H17B 0.3999 0.6093 0.6630 0.065 Uiso calc R 1 . .
    H H17C 0.3768 0.5612 0.7237 0.065 Uiso calc R 1 . .
    C C15 0.9036(3) 0.3855(2) 0.64991(10) 0.0382(6) Uani d . 1 . .
    H H15A 0.8431 0.4102 0.6809 0.057 Uiso calc R 1 . .
    H H15B 0.9868 0.4281 0.6430 0.057 Uiso calc R 1 . .
    H H15C 0.9411 0.3232 0.6601 0.057 Uiso calc R 1 . .
    C C14 0.2395(3) 0.12913(18) 0.55544(10) 0.0382(6) Uani d . 1 . .
    H H14A 0.1977 0.1924 0.5516 0.057 Uiso calc R 1 . .
    H H14B 0.1594 0.0831 0.5583 0.057 Uiso calc R 1 . .
    H H14C 0.3003 0.1148 0.5222 0.057 Uiso calc R 1 . .
    C C16 0.2646(3) 0.23321(17) 0.71690(10) 0.0427(6) Uani d . 1 . .
    H H16A 0.3452 0.2365 0.7445 0.064 Uiso calc R 1 . .
    H H16B 0.2552 0.1686 0.7029 0.064 Uiso calc R 1 . .
    H H16C 0.1721 0.2524 0.7350 0.064 Uiso calc R 1 . .
loop_
    _atom_site_aniso_label
    _atom_site_aniso_U_11
    _atom_site_aniso_U_22
    _atom_site_aniso_U_33
    _atom_site_aniso_U_12
    _atom_site_aniso_U_13
    _atom_site_aniso_U_23
    O2 0.0365(9) 0.0286(8) 0.0265(8) -0.0083(7) -0.0003(7) 0.0009(7)
    O1 0.0278(8) 0.0357(8) 0.0244(8) -0.0046(7) 0.0007(6) 0.0002(7)
    O3 0.0385(9) 0.0344(9) 0.0292(9) 0.0067(8) 0.0023(7) -0.0034(7)
    C4 0.0283(11) 0.0256(11) 0.0208(11) 0.0011(9) -0.0019(8) 0.0030(9)
    C2 0.0239(10) 0.0329(12) 0.0224(12) -0.0005(9) 0.0010(8) 0.0024(10)
    C1 0.0284(10) 0.0243(11) 0.0194(11) 0.0012(9) -0.0028(8) 0.0035(9)
    C9 0.0309(11) 0.0291(12) 0.0178(10) 0.0024(9) 0.0001(8) 0.0027(9)
    C5 0.0266(10) 0.0245(11) 0.0194(11) 0.0015(9) -0.0014(8) 0.0034(9)
    C7 0.0318(11) 0.0236(11) 0.0226(11) -0.0019(9) -0.0018(9) 0.0035(9)
    C3 0.0249(10) 0.0276(12) 0.0247(11) -0.0038(9) -0.0004(9) 0.0030(9)
    C10 0.0255(11) 0.0286(11) 0.0221(10) -0.0008(9) -0.0006(8) 0.0050(10)
    C6 0.0255(10) 0.0256(11) 0.0218(11) -0.0024(9) -0.0023(9) 0.0020(9)
    C11 0.0412(13) 0.0235(11) 0.0288(12) 0.0012(10) 0.0022(10) 0.0005(10)
    C8 0.0346(11) 0.0261(11) 0.0193(11) 0.0031(9) -0.0015(9) 0.0048(9)
    C13 0.0316(12) 0.0336(13) 0.0289(12) 0.0051(10) 0.0021(9) -0.0043(10)
    C12 0.0504(14) 0.0315(13) 0.0243(12) 0.0103(11) -0.0012(10) 0.0012(11)
    C17 0.0602(16) 0.0371(14) 0.0318(14) 0.0160(12) -0.0048(12) -0.0012(12)
    C15 0.0364(13) 0.0429(14) 0.0354(14) -0.0068(11) -0.0038(11) -0.0004(12)
    C14 0.0303(12) 0.0498(16) 0.0346(14) -0.0090(11) -0.0032(10) 0.0045(12)
    C16 0.0480(14) 0.0448(15) 0.0354(13) -0.0002(12) 0.0158(12) -0.0041(12)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
    _geom_bond_atom_site_label_1
    _geom_bond_atom_site_label_2
    _geom_bond_site_symmetry_2
    _geom_bond_distance
    _geom_bond_publ_flag
    O2 C7 . 1.388(2) ?
    O2 C15 . 1.436(3) ?
    O1 C10 . 1.388(2) ?
    O1 C14 . 1.433(3) ?
    O3 C12 . 1.429(3) ?
    O3 C13 . 1.435(3) ?
    C4 C7 . 1.415(3) ?
    C4 C3 . 1.421(3) ?
    C4 C5 . 1.419(3) ?
    C2 C3 . 1.364(3) ?
    C2 C1 . 1.416(3) ?
    C2 H2 . 0.9300 ?
    C1 C6 . 1.382(3) ?
    C1 C1 3_556 1.480(4) ?
    C9 C10 . 1.378(3) ?
    C9 C8 . 1.421(3) ?
    C9 C13 . 1.518(3) ?
    C5 C6 . 1.408(3) ?
    C5 C10 . 1.418(3) ?
    C7 C8 . 1.373(3) ?
    C3 H3 . 0.9300 ?
    C6 H6 . 0.9300 ?
    C11 C8 . 1.509(3) ?
    C11 C12 . 1.523(3) ?
    C11 H11A . 0.9700 ?
    C11 H11B . 0.9700 ?
    C13 C16 . 1.508(3) ?
    C13 H13 . 0.9800 ?
    C12 C17 . 1.505(3) ?
    C12 H12 . 0.9800 ?
    C17 H17A . 0.9600 ?
    C17 H17B . 0.9600 ?
    C17 H17C . 0.9600 ?
    C15 H15A . 0.9600 ?
    C15 H15B . 0.9600 ?
    C15 H15C . 0.9600 ?
    C14 H14A . 0.9600 ?
    C14 H14B . 0.9600 ?
    C14 H14C . 0.9600 ?
    C16 H16A . 0.9600 ?
    C16 H16B . 0.9600 ?
    C16 H16C . 0.9600 ?
loop_
    _geom_angle_atom_site_label_1
    _geom_angle_atom_site_label_2
    _geom_angle_atom_site_label_3
    _geom_angle_site_symmetry_1
    _geom_angle_site_symmetry_3
    _geom_angle
    _geom_angle_publ_flag
    C7 O2 C15 . . 113.58(16) ?
    C10 O1 C14 . . 113.67(15) ?
    C12 O3 C13 . . 114.47(16) ?
    C7 C4 C3 . . 123.47(19) ?
    C7 C4 C5 . . 118.55(18) ?
    C3 C4 C5 . . 117.97(18) ?
    C3 C2 C1 . . 121.43(18) ?
    C3 C2 H2 . . 119.3 ?
    C1 C2 H2 . . 119.3 ?
    C6 C1 C2 . . 118.01(18) ?
    C6 C1 C1 . 3_556 118.94(14) ?
    C2 C1 C1 . 3_556 123.03(14) ?
    C10 C9 C8 . . 119.23(18) ?
    C10 C9 C13 . . 119.07(19) ?
    C8 C9 C13 . . 121.64(19) ?
    C6 C5 C10 . . 121.61(19) ?
    C6 C5 C4 . . 119.37(18) ?
    C10 C5 C4 . . 119.02(18) ?
    C8 C7 O2 . . 120.66(18) ?
    C8 C7 C4 . . 121.54(19) ?
    O2 C7 C4 . . 117.67(18) ?
    C2 C3 C4 . . 121.19(19) ?
    C2 C3 H3 . . 119.4 ?
    C4 C3 H3 . . 119.4 ?
    C9 C10 O1 . . 120.42(18) ?
    C9 C10 C5 . . 121.46(19) ?
    O1 C10 C5 . . 118.11(18) ?
    C1 C6 C5 . . 122.02(19) ?
    C1 C6 H6 . . 119.0 ?
    C5 C6 H6 . . 119.0 ?
    C8 C11 C12 . . 109.3(2) ?
    C8 C11 H11A . . 109.8 ?
    C12 C11 H11A . . 109.8 ?
    C8 C11 H11B . . 109.8 ?
    C12 C11 H11B . . 109.8 ?
    H11A C11 H11B . . 108.3 ?
    C7 C8 C9 . . 120.13(19) ?
    C7 C8 C11 . . 121.99(19) ?
    C9 C8 C11 . . 117.76(19) ?
    O3 C13 C16 . . 105.14(17) ?
    O3 C13 C9 . . 113.29(18) ?
    C16 C13 C9 . . 113.37(19) ?
    O3 C13 H13 . . 108.3 ?
    C16 C13 H13 . . 108.3 ?
    C9 C13 H13 . . 108.3 ?
    O3 C12 C17 . . 107.21(19) ?
    O3 C12 C11 . . 107.70(18) ?
    C17 C12 C11 . . 113.7(2) ?
    O3 C12 H12 . . 109.4 ?
    C17 C12 H12 . . 109.4 ?
    C11 C12 H12 . . 109.4 ?
    C12 C17 H17A . . 109.5 ?
    C12 C17 H17B . . 109.5 ?
    H17A C17 H17B . . 109.5 ?
    C12 C17 H17C . . 109.5 ?
    H17A C17 H17C . . 109.5 ?
    H17B C17 H17C . . 109.5 ?
    O2 C15 H15A . . 109.5 ?
    O2 C15 H15B . . 109.5 ?
    H15A C15 H15B . . 109.5 ?
    O2 C15 H15C . . 109.5 ?
    H15A C15 H15C . . 109.5 ?
    H15B C15 H15C . . 109.5 ?
    O1 C14 H14A . . 109.5 ?
    O1 C14 H14B . . 109.5 ?
    H14A C14 H14B . . 109.5 ?
    O1 C14 H14C . . 109.5 ?
    H14A C14 H14C . . 109.5 ?
    H14B C14 H14C . . 109.5 ?
    C13 C16 H16A . . 109.5 ?
    C13 C16 H16B . . 109.5 ?
    H16A C16 H16B . . 109.5 ?
    C13 C16 H16C . . 109.5 ?
    H16A C16 H16C . . 109.5 ?
    H16B C16 H16C . . 109.5 ?
data_global
_journal_date_recd_electronic     2008-02-22
_journal_date_accepted     2008-03-19
_journal_name_full     'Acta Crystallographica, Section E'
_journal_year     2008
_journal_volume     64
_journal_issue      4
_journal_page_first     o758
_journal_page_last     o758
_journal_paper_category     QO
_journal_coeditor_code     BI2283
_publ_contact_author_name     'Margaret A. Brimble'
_publ_contact_author_address
;
Department of Chemistry
University of Auckland
Private Bag 92019
Auckland
New Zealand
;
_publ_contact_author_email     'm.brimble@auckland.ac.nz'
_publ_contact_author_fax     '+64 9 3737422'
_publ_contact_author_phone     '+64 9 3737599 ext. 88259'
_publ_section_title
;\
(1R,1'R,3S,3'S)-5,5',10,10'-Tetramethoxy-1,1',3,3'-\
tetramethyl-3,3',4,4'-tetrahydro-1H,1'H-8,8'-\
bi[benzo[g]isochromene]
;
loop_
    _publ_author_name
    _publ_author_footnote
    _publ_author_address
    'Sejberg, Jimmy J. P.' .
;
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland,
New Zealand
;
    'Sperry, Jonathan' .
;
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland,
New Zealand
;
    'Choi, Ka Wai' .
;
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland,
New Zealand
;
    'Boyd, Peter D. W.' .
;
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland,
New Zealand
;
    'Brimble, Margaret A.' .
;
Department of Chemistry, University of Auckland, Private Bag 92019, Auckland,
New Zealand
;
_exptl_special_details
;
[α]D²⁴+36.2 (c 0.12, CH₂Cl₂);
υₘₐₓ(CH₂Cl₂)/cm⁻¹ 3418, 3053, 2986, 1638, 1421, 1264, 733;
δ~H ~(300 MHz, CDCl₃) 1.44 (6 H, d, ³JHH 6.0,
2\\timesCHCH₃), 1.73 (6 H, d, ³JHH 6.6,
2\\timesCHCH₃), 2.66 (2 H, dd, ²JHH 16.2, ³JHH
 11.0, 2\\timesCHH), 3.11 (2 H, dd, ²JHH 16.2,
³JHH 1.5, 2\\timesCHH), 3.74 (2 H, m,
2\\timesCHCH₃), 3.91 (6 H, s, 2\\timesOCH₃), 3.95 (6 H, s,
2\\timesOCH₃), 5.26 (2 H, q, ³J~HH ~6.6, 2\\timesCHCH₃),
7.89 (2 H, dd, ³J~HH ~8.8, ⁴JHH 1.6, Ar-H), 8.18 (2 H, d,
³J~HH ~8.8, Ar-H), 8.37 (2 H, d, ⁴J~HH ~1.6, Ar-H); δC(75
MHz, CDCl₃) 21.8 (2\\timesCHCH₃), 22.4 (2\\timesCHCH₃),
32.0 (2\\timesCH₂), 61.1 (2\\timesOMe), 61.4 (2\\timesOMe), 69.6
(2\\timesCH), 71.3 (2\\timesCH), 120.4 (2\\timesCH arom), 122.8 (2\\timesCH
arom), 125.5 (2\\timesC arom), 125.7 (2\\timesCH arom), 126.6 (2\\timesC
arom), 127.7 (2\\timesC arom), 129.9 (2\\timesC arom), 138.3 (2\\timesC arom),
148.8 (2\\timesC arom), 149.0 (2\\timesC arom); m/z (EI) 542 (100%,
[M]⁺), 527 (39), 199 (22), 105 (32), 57 (40), 44 (72); HRMS (EI, [M]⁺)
Found 542.26673 Calc. for C~34~H~38~O~6 ~542.26684.
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